Sukhinder Singh Cassidy: Either You Manage Me or I Manage You

This interview with Sukhinder Singh Cassidy was conducted and condensed by Adam Bryant. Ms. Singh Cassidy is the founder and chairman of Joyus, a video shopping site, and a founder of theBoardlist.com, which aims to put more women on boards.

Q. What were your early years like?

A. I was hyper-intense, hyper-academic and a pretty uptight kid.

I remember hating going to Brownies, and I always felt slightly out of sorts there, so I quit. But then I locked myself in the bathroom at home and cried. And my mom asked, “Why are you so upset?” It was from feeling guilty that I quit. Ultimately I went back and finished Brownies and did a year of Girl Guides, and then I quit.

Why did you go back if you didn’t like it?

It was conscientiousness and guilt from not having followed through on something. It was feeling that if I’m going to quit, I can’t quit this way. I still think of myself as a conscientious person.

Tell me about your parents.

They’re both doctors, and my father loved running his medical practice as a business.

Early on, he taught us all how to do his ledgers and his income taxes. I was doing his income taxes when I was about 10 or 11, and then as a teenager I built a system to do his ledgers on the computer.

He always would say to me when I was young, “You should work for yourself.” By the time I was about 25, I wanted to start a business.

It seems you were driven from an early age.

I’m just wired that way. If anything, I wish there were days I could dial down my intensity. I’ve always wanted to do more.

And my parents were always highly conscientious. Their work ethic was incredible. They immigrated to Canada when they were older and had to restart their medical careers.

What were your college years like?

Interestingly, college was my revolt period after growing up in a highly conservative household. So when I went away to college, I was going to have a good time. My grades were good, but I was mostly enjoying the freedom to make my own choices.

Your first job was on Wall Street. Was your compass always pointed there?

My compass was not pointed anywhere. Interestingly, for somebody who was so intense, I actually didn’t know what I wanted to do. I went through a recruiting cycle after graduating but didn’t get a job. So I went from feeling great about myself as a high school student to wondering what’s wrong with me. I felt pretty demoralized. It really made me question myself. Then I interviewed at Merrill Lynch, and the hiring process went really fast.

So now I tell college grads, you’re going to end up where you’re supposed to be. In hindsight, why did Merrill work? In some ways, it’s very clear. I’m aggressive; Merrill is aggressive. I’m intense; Merrill is intense. I don’t come wrapped up in this nice neat bow, and so why was I surprised that the more conservative places didn’t hire me?

You have worked at a lot of companies, including Google, Amazon, BSkyB. It seems you like new challenges.

I’ve learned that my risk tolerance is high. Partly it comes from having had to figure out that time after college when I was having trouble getting hired. And then it finally worked.

I always say to people, once you realize you’re employable, everything else is O.K. I’m always willing to let go of something before the next thing shows up because I have the sense that I could put food on the table.

The other part of it is that I’m very impatient. Whenever I think I’m stagnating and not going to get where I’m meant to go, I have this anxiety. So the anxiety of not getting there overwhelms the fear of uncertainty. So I guess I just trade one fear for another. People see that as risk tolerance, but it’s more this sense that I’m supposed to contribute something more or learn something more.

Early leadership lessons?

I’ve learned to have a little bit of distance from the people I manage, and I don’t feel the need that they all need to be at my house for dinner every weekend. On the other hand, I feel they’re pretty sure that I am emotionally committed to them and emotionally invested in making them successful. When people feel you’re all in on the company and on them, they will forgive a lot of imperfections and errors. It’s really about authenticity.

I also have this philosophy now, which I tell my team all the time, of, “Either you manage me or I manage you. Which would you prefer?”

I like to give people a lot of rope. I like to see what they can do, but I also have an amazing capacity for detail. I know what they said they were going to do, and if they’re not doing it, what’s happening? Then I’m starting to pull the rope back.

And if I’m starting to manage your time, you’re not at your best, and I’m not at my best. Because when I’m managing your time with the opinions I have, I’m going to start telling you what to do, right? I’d rather bring my vision collaboratively with somebody else’s vision. But if you show up with no vision, you’re going to walk out with my vision, which I don’t think is a very empowering place to be.

How do you hire?

I love really smart people, but I love really smart people who are focused on the good of the company before themselves. That gets my respect like nothing else. It’s a unique combination to find somebody who is so capable and smart, but has some level of humility about their place in the entire ecosystem. I’ve dealt with a lot of people who are really smart, but it’s all about them. And that’s a very frustrating place for me.

I also always ask people what drains their energy, and what gives them energy. That tells me a lot about what people like to do and what they’re good at.

Each week, Adam Bryant talks with top executives about leadership. Follow him on Twitter: @nytcorneroffice. This interview has been edited for space and clarity.

A version of this article appears in print on , on Page BU2 of the New York edition with the headline: Either You Manage Me or I Manage You. Order Reprints | Today’s Paper | Subscribe

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